NP-MRD: Showing NP-Card for 22-acetylisocyclocitrinol A (NP0004977)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2020-12-09 02:21:26 UTC

Updated at

2021-07-15 16:50:42 UTC

NP-MRD ID

NP0004977

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-acetylisocyclocitrinol A

Provided By

NPAtlas

Description

(3S)-2-hydroxy-2-[(2R,5S,6S,9R,13S,15S)-15-hydroxy-5-methyl-12-oxotetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]Octadeca-1(17),10-dien-6-yl]hex-4-en-3-yl acetate belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). 22-acetylisocyclocitrinol A is found in Penicillium citrinum. 22-acetylisocyclocitrinol A was first documented in 2003 (PMID: 14602008). Based on a literature review very few articles have been published on (3S)-2-hydroxy-2-[(2R,5S,6S,9R,13S,15S)-15-hydroxy-5-methyl-12-oxotetracyclo[11.4.1.0²,¹⁰.0⁵,⁹]Octadeca-1(17),10-dien-6-yl]hex-4-en-3-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118153D          

 70 73  0  0  0  0            999 V2000
    5.2860   -1.2279    3.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192   -0.6314    1.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478   -1.2577    1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -0.6140   -0.3317 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2749    0.1639   -0.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1004   -0.2431   -1.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3479    0.5159   -1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8611   -1.2475   -2.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    0.2488   -0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0586    1.3636    0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600    0.8524   -1.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6494   -0.5636   -0.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4972   -1.4280    0.9809 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0136   -1.4746    1.2854 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5747   -1.0802   -0.0363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9688   -0.6823   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516   -1.0499    0.9651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0382   -0.8510    1.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5162   -1.7088    2.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    0.2018    0.9927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2053    1.3230    0.3405 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7571    0.7370   -0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4776    0.6765   -2.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9679    0.6925   -2.2285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6523    0.5348   -0.8999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9551    1.7474   -0.2954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9431   -0.4330   -0.0228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4564    0.0939   -1.2645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4456    1.1733   -1.6231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0566    0.5753   -1.6995 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3386    0.1350   -0.3269 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0516    1.1223    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -1.6444    3.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5192   -1.9745    3.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2122   -0.4083    4.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3904    0.3609    1.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9980   -2.2546    1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0795   -1.4227   -1.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2005    1.1446   -2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6359    1.1067   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1626   -0.2364   -2.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3881    2.2333    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1112    1.0760    1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.7997    0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0149    0.1563   -2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -1.2768   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0138   -1.0651    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -2.5129    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -0.7860    2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3149   -2.4938    1.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -1.8620   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -1.6427    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5884    0.5287    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7480    2.2589    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3067    1.5284    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    0.5998   -2.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2441   -0.0990   -2.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2576    1.6747   -2.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6608    0.0799   -1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0428    1.6999    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4200   -1.1709   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6863   -1.0038    0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192   -0.5771   -2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    1.9853   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    1.5500   -2.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -0.3582   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.2154   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870    0.9567    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163    0.9868    1.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    2.1830    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 12  1  0  0  0  0
 31 15  1  0  0  0  0
 28 16  1  0  0  0  0
 27 20  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  2 36  1  0  0  0  0
  3 37  1  0  0  0  0
  4 38  1  6  0  0  0
  7 39  1  0  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
 10 44  1  0  0  0  0
 11 45  1  0  0  0  0
 12 46  1  6  0  0  0
 13 47  1  0  0  0  0
 13 48  1  0  0  0  0
 14 49  1  0  0  0  0
 14 50  1  0  0  0  0
 15 51  1  6  0  0  0
 17 52  1  0  0  0  0
 20 53  1  1  0  0  0
 21 54  1  0  0  0  0
 21 55  1  0  0  0  0
 23 56  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 25 59  1  6  0  0  0
 26 60  1  0  0  0  0
 27 61  1  0  0  0  0
 27 62  1  0  0  0  0
 28 63  1  6  0  0  0
 29 64  1  0  0  0  0
 29 65  1  0  0  0  0
 30 66  1  0  0  0  0
 30 67  1  0  0  0  0
 32 68  1  0  0  0  0
 32 69  1  0  0  0  0
 32 70  1  0  0  0  0
M  END

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    5.2860   -1.2279    3.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192   -0.6314    1.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478   -1.2577    1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -0.6140   -0.3317 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2749    0.1639   -0.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1004   -0.2431   -1.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3479    0.5159   -1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8611   -1.2475   -2.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    0.2488   -0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0586    1.3636    0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600    0.8524   -1.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6494   -0.5636   -0.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4972   -1.4280    0.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.4746    1.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -1.0802   -0.0363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9688   -0.6823   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516   -1.0499    0.9651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0382   -0.8510    1.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5162   -1.7088    2.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    0.2018    0.9927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2053    1.3230    0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571    0.7370   -0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4776    0.6765   -2.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9679    0.6925   -2.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6523    0.5348   -0.8999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9551    1.7474   -0.2954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9431   -0.4330   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4564    0.0939   -1.2645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4456    1.1733   -1.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0566    0.5753   -1.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386    0.1350   -0.3269 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0516    1.1223    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -1.6444    3.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5192   -1.9745    3.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2122   -0.4083    4.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3904    0.3609    1.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9980   -2.2546    1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0795   -1.4227   -1.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2005    1.1446   -2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6359    1.1067   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1626   -0.2364   -2.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3881    2.2333    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1112    1.0760    1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.7997    0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0149    0.1563   -2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -1.2768   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0138   -1.0651    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -2.5129    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -0.7860    2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3149   -2.4938    1.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -1.8620   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -1.6427    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5884    0.5287    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7480    2.2589    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3067    1.5284    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    0.5998   -2.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2441   -0.0990   -2.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2576    1.6747   -2.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6608    0.0799   -1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0428    1.6999    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4200   -1.1709   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6863   -1.0038    0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192   -0.5771   -2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    1.9853   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    1.5500   -2.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -0.3582   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.2154   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870    0.9567    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163    0.9868    1.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    2.1830    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  4  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 12  1  0
 31 15  1  0
 28 16  1  0
 27 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  4 38  1  6
  7 39  1  0
  7 40  1  0
  7 41  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  6
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  6
 17 52  1  0
 20 53  1  1
 21 54  1  0
 21 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  6
 26 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  6
 29 64  1  0
 29 65  1  0
 30 66  1  0
 30 67  1  0
 32 68  1  0
 32 69  1  0
 32 70  1  0
M  END


  Mrv1652306242118153D          

 70 73  0  0  0  0            999 V2000
    5.2860   -1.2279    3.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192   -0.6314    1.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478   -1.2577    1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -0.6140   -0.3317 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2749    0.1639   -0.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1004   -0.2431   -1.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3479    0.5159   -1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8611   -1.2475   -2.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    0.2488   -0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0586    1.3636    0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600    0.8524   -1.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6494   -0.5636   -0.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4972   -1.4280    0.9809 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0136   -1.4746    1.2854 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5747   -1.0802   -0.0363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9688   -0.6823   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516   -1.0499    0.9651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0382   -0.8510    1.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5162   -1.7088    2.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    0.2018    0.9927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2053    1.3230    0.3405 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7571    0.7370   -0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4776    0.6765   -2.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9679    0.6925   -2.2285 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6523    0.5348   -0.8999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9551    1.7474   -0.2954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9431   -0.4330   -0.0228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4564    0.0939   -1.2645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4456    1.1733   -1.6231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0566    0.5753   -1.6995 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3386    0.1350   -0.3269 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0516    1.1223    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -1.6444    3.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5192   -1.9745    3.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2122   -0.4083    4.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3904    0.3609    1.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9980   -2.2546    1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0795   -1.4227   -1.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2005    1.1446   -2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6359    1.1067   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1626   -0.2364   -2.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3881    2.2333    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1112    1.0760    1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.7997    0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0149    0.1563   -2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -1.2768   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0138   -1.0651    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -2.5129    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -0.7860    2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3149   -2.4938    1.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -1.8620   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -1.6427    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5884    0.5287    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7480    2.2589    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3067    1.5284    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    0.5998   -2.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2441   -0.0990   -2.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2576    1.6747   -2.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6608    0.0799   -1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0428    1.6999    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4200   -1.1709   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6863   -1.0038    0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192   -0.5771   -2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    1.9853   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    1.5500   -2.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -0.3582   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.2154   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870    0.9567    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163    0.9868    1.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    2.1830    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 12  1  0  0  0  0
 31 15  1  0  0  0  0
 28 16  1  0  0  0  0
 27 20  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  2 36  1  0  0  0  0
  3 37  1  0  0  0  0
  4 38  1  6  0  0  0
  7 39  1  0  0  0  0
  7 40  1  0  0  0  0
  7 41  1  0  0  0  0
 10 42  1  0  0  0  0
 10 43  1  0  0  0  0
 10 44  1  0  0  0  0
 11 45  1  0  0  0  0
 12 46  1  6  0  0  0
 13 47  1  0  0  0  0
 13 48  1  0  0  0  0
 14 49  1  0  0  0  0
 14 50  1  0  0  0  0
 15 51  1  6  0  0  0
 17 52  1  0  0  0  0
 20 53  1  1  0  0  0
 21 54  1  0  0  0  0
 21 55  1  0  0  0  0
 23 56  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 25 59  1  6  0  0  0
 26 60  1  0  0  0  0
 27 61  1  0  0  0  0
 27 62  1  0  0  0  0
 28 63  1  6  0  0  0
 29 64  1  0  0  0  0
 29 65  1  0  0  0  0
 30 66  1  0  0  0  0
 30 67  1  0  0  0  0
 32 68  1  0  0  0  0
 32 69  1  0  0  0  0
 32 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004977

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C([H])=C2C([H])([H])[C@]([H])(C(=O)C([H])=C3[C@]4([H])C([H])([H])C([H])([H])[C@]([H])([C@@](O[H])(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C(\[H])=C(/[H])C([H])([H])[H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])[C@]23[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O5/c1-5-6-25(32-16(2)28)27(4,31)24-10-9-22-21-15-23(30)18-13-17(7-8-19(29)14-18)20(21)11-12-26(22,24)3/h5-7,15,18-20,22,24-25,29,31H,8-14H2,1-4H3/b6-5+/t18-,19-,20+,22-,24-,25-,26-,27-/m0/s1

> <INCHI_KEY>
IZVFLWXSSIJELF-RLEDVZOJSA-N

> <FORMULA>
C27H38O5

> <MOLECULAR_WEIGHT>
442.596

> <EXACT_MASS>
442.271924324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.7842646610069

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4E)-2-hydroxy-2-[(2R,5S,6S,9R,13S,15S)-15-hydroxy-5-methyl-12-oxotetracyclo[11.4.1.0^{2,10}.0^{5,9}]octadeca-1(17),10-dien-6-yl]hex-4-en-3-yl acetate

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
3.4017383176666667

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.19453697489515

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.709867467084788

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7202284119989324

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
126.24449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4E)-2-hydroxy-2-[(2R,5S,6S,9R,13S,15S)-15-hydroxy-5-methyl-12-oxotetracyclo[11.4.1.0^{2,10}.0^{5,9}]octadeca-1(17),10-dien-6-yl]hex-4-en-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    5.2860   -1.2279    3.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192   -0.6314    1.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478   -1.2577    1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -0.6140   -0.3317 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2749    0.1639   -0.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1004   -0.2431   -1.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3479    0.5159   -1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8611   -1.2475   -2.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    0.2488   -0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0586    1.3636    0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600    0.8524   -1.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6494   -0.5636   -0.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4972   -1.4280    0.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.4746    1.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -1.0802   -0.0363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9688   -0.6823   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516   -1.0499    0.9651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0382   -0.8510    1.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5162   -1.7088    2.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    0.2018    0.9927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2053    1.3230    0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571    0.7370   -0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4776    0.6765   -2.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9679    0.6925   -2.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6523    0.5348   -0.8999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9551    1.7474   -0.2954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9431   -0.4330   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4564    0.0939   -1.2645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4456    1.1733   -1.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0566    0.5753   -1.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386    0.1350   -0.3269 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0516    1.1223    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -1.6444    3.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5192   -1.9745    3.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2122   -0.4083    4.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3904    0.3609    1.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9980   -2.2546    1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0795   -1.4227   -1.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2005    1.1446   -2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6359    1.1067   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1626   -0.2364   -2.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3881    2.2333    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1112    1.0760    1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.7997    0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0149    0.1563   -2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -1.2768   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0138   -1.0651    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -2.5129    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -0.7860    2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3149   -2.4938    1.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -1.8620   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -1.6427    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5884    0.5287    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7480    2.2589    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3067    1.5284    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    0.5998   -2.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2441   -0.0990   -2.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2576    1.6747   -2.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6608    0.0799   -1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0428    1.6999    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4200   -1.1709   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6863   -1.0038    0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192   -0.5771   -2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    1.9853   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    1.5500   -2.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -0.3582   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.2154   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870    0.9567    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163    0.9868    1.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    2.1830    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  4  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 12  1  0
 31 15  1  0
 28 16  1  0
 27 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  4 38  1  6
  7 39  1  0
  7 40  1  0
  7 41  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  6
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  6
 17 52  1  0
 20 53  1  1
 21 54  1  0
 21 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  6
 26 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  6
 29 64  1  0
 29 65  1  0
 30 66  1  0
 30 67  1  0
 32 68  1  0
 32 69  1  0
 32 70  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       5.286  -1.228   3.299  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.019  -0.631   1.968  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.348  -1.258   1.010  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.097  -0.614  -0.332  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.275   0.164  -0.568  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.100  -0.243  -1.600  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.348   0.516  -1.910  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.861  -1.248  -2.321  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.864   0.249  -0.339  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.059   1.364   0.616  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.860   0.852  -1.632  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.649  -0.564  -0.242  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.497  -1.428   0.981  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.014  -1.475   1.285  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.575  -1.080  -0.036  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.969  -0.682  -0.070  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.652  -1.050   0.965  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.038  -0.851   1.363  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.516  -1.709   2.158  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.007   0.202   0.993  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.205   1.323   0.341  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.757   0.737  -0.955  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.478   0.677  -2.065  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.968   0.693  -2.228  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.652   0.535  -0.900  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.955   1.747  -0.295  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.943  -0.433  -0.023  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.456   0.094  -1.264  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.446   1.173  -1.623  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.057   0.575  -1.700  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.339   0.135  -0.327  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.052   1.122   0.753  0.00  0.00           C+0
HETATM   33  H   UNK     0       6.313  -1.644   3.316  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.519  -1.974   3.579  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.212  -0.408   4.048  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.390   0.361   1.760  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.998  -2.255   1.237  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.080  -1.423  -1.052  0.00  0.00           H+0
HETATM   39  H   UNK     0       7.200   1.145  -2.807  0.00  0.00           H+0
HETATM   40  H   UNK     0       7.636   1.107  -1.024  0.00  0.00           H+0
HETATM   41  H   UNK     0       8.163  -0.236  -2.082  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.388   2.233   0.448  0.00  0.00           H+0
HETATM   43  H   UNK     0       3.111   1.076   1.685  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.080   1.800   0.391  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.015   0.156  -2.321  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.663  -1.277  -1.122  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.014  -1.065   1.867  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.724  -2.513   0.740  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.273  -0.786   2.111  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.315  -2.494   1.613  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.301  -1.862  -0.772  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.123  -1.643   1.744  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.588   0.529   1.853  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.748   2.259   0.245  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.307   1.528   0.961  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.882   0.600  -2.980  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.244  -0.099  -2.952  0.00  0.00           H+0
HETATM   58  H   UNK     0      -6.258   1.675  -2.694  0.00  0.00           H+0
HETATM   59  H   UNK     0      -7.661   0.080  -1.142  0.00  0.00           H+0
HETATM   60  H   UNK     0      -7.043   1.700   0.668  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.420  -1.171  -0.665  0.00  0.00           H+0
HETATM   62  H   UNK     0      -6.686  -1.004   0.566  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.519  -0.577  -2.149  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.550   1.985  -0.906  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.762   1.550  -2.636  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.166  -0.358  -2.320  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.640   1.215  -2.222  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.987   0.957   1.171  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.716   0.987   1.625  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.003   2.183   0.396  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3   36                                                  
CONECT    3    2    4   37                                                  
CONECT    4    3    5    9   38                                             
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6   39   40   41                                             
CONECT    8    6                                                            
CONECT    9    4   10   11   12                                             
CONECT   10    9   42   43   44                                             
CONECT   11    9   45                                                       
CONECT   12    9   13   31   46                                             
CONECT   13   12   14   47   48                                             
CONECT   14   13   15   49   50                                             
CONECT   15   14   16   31   51                                             
CONECT   16   15   17   28                                                  
CONECT   17   16   18   52                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   27   53                                             
CONECT   21   20   22   54   55                                             
CONECT   22   21   23   28                                                  
CONECT   23   22   24   56                                                  
CONECT   24   23   25   57   58                                             
CONECT   25   24   26   27   59                                             
CONECT   26   25   60                                                       
CONECT   27   25   20   61   62                                             
CONECT   28   22   29   16   63                                             
CONECT   29   28   30   64   65                                             
CONECT   30   29   31   66   67                                             
CONECT   31   30   32   12   15                                             
CONECT   32   31   68   69   70                                             
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    2                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    7                                                            
CONECT   42   10                                                            
CONECT   43   10                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   17                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   21                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   29                                                            
CONECT   65   29                                                            
CONECT   66   30                                                            
CONECT   67   30                                                            
CONECT   68   32                                                            
CONECT   69   32                                                            
CONECT   70   32                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  146    0
END

RDKit          3D

70 73  0  0  0  0  0  0  0  0999 V2000
    5.2860   -1.2279    3.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0192   -0.6314    1.9682 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478   -1.2577    1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -0.6140   -0.3317 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2749    0.1639   -0.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1004   -0.2431   -1.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3479    0.5159   -1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8611   -1.2475   -2.3209 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8644    0.2488   -0.3388 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0586    1.3636    0.6157 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8600    0.8524   -1.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6494   -0.5636   -0.2422 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4972   -1.4280    0.9809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.4746    1.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5747   -1.0802   -0.0363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9688   -0.6823   -0.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516   -1.0499    0.9651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0382   -0.8510    1.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5162   -1.7088    2.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    0.2018    0.9927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2053    1.3230    0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571    0.7370   -0.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4776    0.6765   -2.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9679    0.6925   -2.2285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6523    0.5348   -0.8999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9551    1.7474   -0.2954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9431   -0.4330   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4564    0.0939   -1.2645 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4456    1.1733   -1.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0566    0.5753   -1.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386    0.1350   -0.3269 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0516    1.1223    0.7529 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -1.6444    3.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5192   -1.9745    3.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2122   -0.4083    4.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3904    0.3609    1.7603 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9980   -2.2546    1.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0795   -1.4227   -1.0521 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2005    1.1446   -2.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6359    1.1067   -1.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1626   -0.2364   -2.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3881    2.2333    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1112    1.0760    1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.7997    0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0149    0.1563   -2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6625   -1.2768   -1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0138   -1.0651    1.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7244   -2.5129    0.7397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2733   -0.7860    2.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3149   -2.4938    1.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -1.8620   -0.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1233   -1.6427    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5884    0.5287    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7480    2.2589    0.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3067    1.5284    0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8823    0.5998   -2.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2441   -0.0990   -2.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2576    1.6747   -2.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6608    0.0799   -1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0428    1.6999    0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4200   -1.1709   -0.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6863   -1.0038    0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192   -0.5771   -2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    1.9853   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7618    1.5500   -2.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657   -0.3582   -2.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396    1.2154   -2.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9870    0.9567    1.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163    0.9868    1.6246 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0034    2.1830    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  4  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 22 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  1
 31 12  1  0
 31 15  1  0
 28 16  1  0
 27 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  2 36  1  0
  3 37  1  0
  4 38  1  6
  7 39  1  0
  7 40  1  0
  7 41  1  0
 10 42  1  0
 10 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  6
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  6
 17 52  1  0
 20 53  1  1
 21 54  1  0
 21 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  6
 26 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  6
 29 64  1  0
 29 65  1  0
 30 66  1  0
 30 67  1  0
 32 68  1  0
 32 69  1  0
 32 70  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3S)-2-Hydroxy-2-[(2R,5S,6S,9R,13S,15S)-15-hydroxy-5-methyl-12-oxotetracyclo[11.4.1.0,.0,]octadeca-1(17),10-dien-6-yl]hex-4-en-3-yl acetic acid	Generator

Chemical Formula

C₂₇H₃₈O₅

Average Mass

442.5960 Da

Monoisotopic Mass

442.27192 Da

IUPAC Name

(2S,3S,4E)-2-hydroxy-2-[(2R,5S,6S,9R,13S,15S)-15-hydroxy-5-methyl-12-oxotetracyclo[11.4.1.0^{2,10}.0^{5,9}]octadeca-1(17),10-dien-6-yl]hex-4-en-3-yl acetate

Traditional Name

(2S,3S,4E)-2-hydroxy-2-[(2R,5S,6S,9R,13S,15S)-15-hydroxy-5-methyl-12-oxotetracyclo[11.4.1.0^{2,10}.0^{5,9}]octadeca-1(17),10-dien-6-yl]hex-4-en-3-yl acetate

CAS Registry Number

Not Available

SMILES

C\C=C\[C@H](OC(C)=O)C(C)(O)[C@H]1CC[C@H]2C3=CC(=O)[C@@H]4C[C@@H](O)CC=C(C4)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C27H38O5/c1-5-6-25(32-16(2)28)27(4,31)24-10-9-22-21-15-23(30)18-13-17(7-8-19(29)14-18)20(21)11-12-26(22,24)3/h5-7,15,18-20,22,24-25,29,31H,8-14H2,1-4H3/b6-5+/t18-,19-,20+,22-,24-,25-,26-,27?/m0/s1

InChI Key

IZVFLWXSSIJELF-RLEDVZOJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium citrinum	NPAtlas	14602008

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.13	ALOGPS
logP	3.4	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	13.71	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.24 m³·mol⁻¹	ChemAxon
Polarizability	50.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA014620

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78438019

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587162

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Amagata T, Amagata A, Tenney K, Valeriote FA, Lobkovsky E, Clardy J, Crews P: Unusual C25 steroids produced by a sponge-derived Penicillium citrinum. Org Lett. 2003 Nov 13;5(23):4393-6. doi: 10.1021/ol0356800. [PubMed:14602008 ]

Showing NP-Card for 22-acetylisocyclocitrinol A (NP0004977)

MOL for NP0004977 (22-acetylisocyclocitrinol A)

3D MOL for NP0004977 (22-acetylisocyclocitrinol A)

3D SDF for NP0004977 (22-acetylisocyclocitrinol A)

3D-SDF for NP0004977 (22-acetylisocyclocitrinol A)

PDB for NP0004977 (22-acetylisocyclocitrinol A)

3D PDB for NP0004977 (22-acetylisocyclocitrinol A)

SMILES for NP0004977 (22-acetylisocyclocitrinol A)

INCHI for NP0004977 (22-acetylisocyclocitrinol A)

Structure for NP0004977 (22-acetylisocyclocitrinol A)

3D Structure for NP0004977 (22-acetylisocyclocitrinol A)